1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

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Chemical Name:1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone
CAS No.:179990-51-3
Molecular Formula:C₂₈H₂₇NO₃
Molecular Weight:425.527
Hs Code.:

Synonyms:1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

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Chemical Property of 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

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Technology Process of 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

There total 8 articles about 1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 917-54-4
methyllithium

: 179990-61-5
(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrole-4-carboxylic acid methyl ester

: 2-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-propan-2-ol

: 179990-51-3
1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

Guidance literature:: With lithium perchlorate; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2.5h;
DOI:10.1021/jo9604245

Reference yield:

: 40216-83-9
L-4-hydroxyproline methyl ester hydrochloride

: 179990-51-3
1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) chlorotrimethylsilane, Et₃N, 2.) Et₃N, Pb(NO₃)2 / 1) CH₂Cl₂, reflux, 1 h; 2) CH₂Cl₂, MeOH, rt, 96 h

2: 100 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -60 °C

3: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h

4: 92 percent / NaBH₄ / methanol; tetrahydrofuran / 4 h / -78 °C

5: 97 percent / PPTS / dimethylformamide; acetone / 24 h / 5 °C

6: 89 percent / LiClO₄ / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C

With sodium tetrahydroborate; chloro-trimethyl-silane; lead(II) nitrate; oxalyl dichloride; MoO₅*pyridine*HMPA; lithium perchlorate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo9604245

Reference yield:

: 55135-66-5
9-bromo-9-phenyl-9H-fluorene

: 179990-51-3
1-[(3aS,4S,6aR)-2,2-Dimethyl-5-(9-phenyl-9H-fluoren-9-yl)-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-4-yl]-ethanone

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) chlorotrimethylsilane, Et₃N, 2.) Et₃N, Pb(NO₃)2 / 1) CH₂Cl₂, reflux, 1 h; 2) CH₂Cl₂, MeOH, rt, 96 h

2: 100 percent / DMSO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -60 °C

3: 1.) NaHMDS, 2.) MoOPH / 1) THF, -78 deg C, 2 h; 2) THF, -78 - -15 deg C, 2.5 h

4: 92 percent / NaBH₄ / methanol; tetrahydrofuran / 4 h / -78 °C

5: 97 percent / PPTS / dimethylformamide; acetone / 24 h / 5 °C

6: 89 percent / LiClO₄ / tetrahydrofuran; diethyl ether / 2.5 h / -78 °C

With sodium tetrahydroborate; chloro-trimethyl-silane; lead(II) nitrate; oxalyl dichloride; MoO₅*pyridine*HMPA; lithium perchlorate; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jo9604245